


Taking Commands

by JackTrades



Series: I Like To Watch [5]
Category: Supernatural
Genre: Dirty Talk, Explicit Sexual Content, F/M, Filthy, M/M, Masturbation, Multi, PWP, Rough Sex, Sex, Sexual harassment of poor Sam by cougars, Threesome, Voyeurism, Wincest - Freeform, slight D/s tone
Language: English
Status: Completed
Published: 2015-11-12
Updated: 2015-11-12
Packaged: 2018-05-01 05:40:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,670
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5194280
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Sam and Dean have some fun while helping Bobby with a case.</p><p>Not necessary to read the rest of the series to read this work.</p>
            </blockquote>





	Taking Commands

**Author's Note:**

> Not necessary to have read the rest of this series but I'm under the impression readers kinda like it so I keep "I Like To Watch" going when I get a decent idea. Inspiration gifs are at the end.
> 
> No beta for me so I own all the mistakes here.

Arguing about it for what seemed like the millionth time in months, yep, that sounds about right for them.  Back in New York, Sam had one of the best and most memorable nights of his life and Dean had a front row seat to the whole thing.  Afterwards they would recall have slightly different recollections of the turn of events, hence the fighting.  According to Dean, Sam needed to get the lead out and he was just doing him a favor; he wasn’t that into it really.  According to Sam, Dean is being stubborn and secretly gets off on the rough sex and refuses to admit it.  The truth actually somewhere in the middle and they both know it.  Damned if either will admit it though. 

This time they were in a motel in Tennessee, slowly packing their stuff after wrapping up a case.  And knocking back a few brews while they researched for a new one.  They always seemed to disagree on the details of that night in New York.  Sam was not letting this drop so easily today, “All I’m saying is that you enjoyed it. Like, a lot. I couldn’t see you most of the time but you were clearly getting off on that woman barking orders at you.” 

“Again, I did it for you and it wasn’t about me.” Dean took a long pull from his bottle of beer.  “Plus you just said it: you couldn’t see me!” 

“You did it for me AND YOU LIKED IT! Why can’t you just admit it?” Sam wanted to grab him by the shoulders and shake him. He had to change tactics. “Look, Dean, it’s okay to have kinks.  I mean… you saw what I did that night and I enjoyed every minute of it.” 

“If I admit I enjoyed it, will you let this drop?” Dean’s temper was about to flare if Sam kept at it. 

“No,” frankly he didn’t care if Dean got pissed, “Because you have given me a ton of shit for this! ‘You’re too rough with girls, Sam,’ ‘You should just be sensual, Sam.’ – ” 

Dean huffed like he was about to blow a gasket when his phone started ringing. He threw a hand up, a clear ‘Shut the fuck up, Sam’ conveyed by it.  He answered.  It was Bobby Singer. 

Bobby had called seemingly out of the blue.  He had a case that required assistance.  And just like that their search for a new case was over.  Needless to say, they hauled ass to get to Bobby – because really? If it had _Bobby_ asking for _help_ it had to be some serious shit! He had them meeting him in Maryland, certainly a long way from where they were used to meeting him.  Rundown motel? That’s their usual.  They were in Bobby’s room where he explained what was going down. It was Sam who was off-put once Bobby explained the finer details of why he called _them_ in particular.  

“Let me get this straight,” Sam was pacing the room and that was never good. “You called us because you need a _distraction_ for some rich women while you hunt this thing down!” 

“We’re not meat, Bobby,” Dean offered condescending but Sam was way too fired up to notice. 

“Yeah!” Sam angrily raked his hands through his hair, “You need our help. We can get it. But we’re not… not… gigolos or something!” 

Bobby was unimpressed with the bluster, “I know that.  Last I checked, Dean over here was giving it away for free…” 

Now Dean was offended, “Hey!” 

Bobby was quick to interject, “Look, boy, I mean nothing by it.  I can’t judge ya.  I’m just saying you’ve acquired a certain reputation over the years… But that ain’t why I called you in – ” 

Dean scoffed, “Reputation?!” 

“As I was saying! You both are more than capable if I can’t contain it,” Bobby was trying to appeal to their hunter sensibilities, “It’s going to be a fairly crowded party.  I need to get through there fairly unnoticed.  I’m just saying, some old guy like me will definitely fly under the radar if you two show up.  I _know_ Dean can turn on the charm if he needs to.” Bobby looked at Sam, who had ceased his pacing to stare a hole in Bobby’s face, “And knowing the way your daddy and your brother as long as I have, I know you can do it too if you want, Sam.” 

Dean gave a bitter laugh, “He’s the black sheep.” He never could resist a good jab. 

Bobby brushed Dean off, “Well, whatever.  He can coast on his good looks then –” 

Sam crossed his arms, “Standing right here, you know!” Dean cracked, snickering at the dig that normally only he could have the balls to give. 

“I’m serious, boys.  I need to be under the radar.  Way under the radar,” Bobby softened his tone hoping to get through to them, “You show up and act charming while I disappear into the background.  Those people will be so busy worrying about fucking you or if their wives are going to fuck you that they won’t notice me poking around. I’ve already got it narrowed down to one of a few items that’ll be at that auction – but let’s face it a guy looking like me ain’t slipping in alone and unnoticed.  We all know a lot of hunters aren’t lookers! Most of them look like they been hit by a shovel a few times! I need someone smart enough to not screw up the hunt and with the people skills to actually keep these people engaged and away from me.” 

Dean leaned back in his chair, “Okay.  I buy your logic…” 

Sam glared at him, “Dean!” 

Dean turned to Sam, “What! It’s true.  Neither of us could get in and out of a place like this, alone, without being conspicuous.” Dean turned to Bobby, “So what do you really need us to do?” 

“Schmooze. Get drunk if you want, hit on a few women,” Bobby raised an eyebrow, “Hell, hit on a few men if that floats your boat! It won’t take much to get them riled up.” 

Dean wasn’t taking the bait, “Fine.” 

Sam was shocked, “What!” 

Dean ignored Sam, “So do you need both of us or just one? Sammy’s got his panties in a bunch about this.” 

Bobby knew how to work this, “Sam can join if he wants to enjoy himself, but otherwise I think you’re perfectly capable, Dean.” 

* * *

Bobby explained his game plan again.  Ill-acquired invites to the silent auction, as father and stepsons, and full tuxedo required for this job.  No gloves or tails or any of that shit, thank god, because Dean can only handle so much fancy, high society nonsense.  After that Sam asked Bobby for copies of his research so that he could familiarize himself with the case in-depth.  He made an excuse to take it back to their room in the motel, about five doors down. Sam was bent about the premise but agreed that him being there would help with Bobby’s cover. And he did owe the man after all he has done for them over the years. 

Dean made stuck around and had a drink with Bobby.  He was usually content to be around Bobby in comfortable silence; he enjoyed the novelty of that because Sam is really the only other person he had that with.  They finished their drinks before Dean went to leave.  Bobby grabbed him by the arm and gave him a serious look, “Is he okay?” 

Dean rolled his eyes, “He’ll get over himself, Bobby.  He just has his own way of dealing with attention from other people…” 

“I’m not talking about the case, idjit!” Bobby could have smacked Dean right now, “I mean is he okay with everything that has happened to him? Your old man and him never really saw eye-to-eye because they’re too stubborn to see what’s in front of them sometimes.  I want to know if he’s handling all of this or if he needs a break.  Or you for that matter.” 

Dean felt that familiar pang that the mention of loss brought to him. He missed John, outright, but Sam was a different story.  Sam had a lot of unresolved issues with their dad that he was never going to get closure on. “I don’t know, to be perfectly honest.  We don’t really… talk about it.  I’m fine though. I miss him, but I’m okay with it.” 

Bobby let that set in.  These boys really were wayward souls, “And what about that girl he was seeing that…” 

Dean let out a heavy, meaningful sigh. “I think he’s got closure on that.  You know, after Yellow Eyes.  I hope so anyway…” 

Bobby couldn’t help but think of his own wife at that second, “And has he let himself be with anyone since? I mean, that you’re aware of?” 

“Only meaningless sex,” Dean forced a laugh, “Not even sure he enjoys it, to be honest. I think he just does it to get me to stop busting his balls most of the time.” 

Bobby clapped a hand on Dean’s shoulder and gave a reassuring squeeze, “Your father was no monk or anything, don’t get me wrong, but Sam and him are more alike that either of them would care to admit.  I just wanna make sure he’s not cutting himself off from the world.” 

Dean gave him a genuine smile, “Not on my watch!” 

Bobby pulled him into a quick hug, “Good!” Then started pushing him towards the door, “Now go read up like your brother is doing! We leave at four o’clock tomorrow.” 

Dean meandered back to his room.  Sometimes he liked to just bask in the comforting feeling that being around Bobby brought.

* * *

 

Four o’clock and they were at the tuxedo rental place.  Dean was never a fan of people poking and measuring him, especially with the measuring tape pushed up against his junk.  It took almost two hours to get all three of them fitted, dressed, and out the door.  

They took the Impala because it looked more in place than Bobby’s car. Dean bitched the entire way about having to valet her.  The gift auction and gala opened doors at six, with silent bids starting at seven. They arrived shortly after seven thirty with Bobby knowing the vengeful spirit was likely tied to one of the estate items on display.  The plan was that he would make a decision on the fly for if it were better to do it early during cocktail hour or wait to sneak away during the dinner. 

As predicted, the second they walked in they could feel eyes on them. Most of the attendees were couples.  None of the women were that unattractive, but the creepy crawling sensation of being undressed by someone’s eyes multiplied by about seven or eight pairs of eyes at a time made Sam feel like he was going to jump out of his skin.  He spoke hastily, “I need a drink,” making a beeline for the open bar.  Dean was on his heels and Bobby started to survey the place. 

A quick scan of the room showed that the items were scattered throughout. Bobby thumbed through the auction guide, “Balls!” One of the drawbacks immediately presented when he saw that all three items he had in mind were nowhere near each other in the display of items.  The one he was most interested in also was smack in the middle of the action… not good. 

At the bar, the younger, heavyset male bartender made eye contact with Sam. He didn’t wait for the bartender to speak, “Two scotches, er, make them doubles.” 

“Any brand preference?” 

Sam was about to take a shot in the dark when Dean strode up, “What label of Johnnie Walker are you serving?” 

“Black. We have Green and Gold for an up-charge.” 

“Black is fine,” both brothers answered in unison.  

The bartender put ice in the glasses then added the scotch.  Dean noted that his nametag said ‘Lee.’ He brought the drinks over and Dean took one, “Thanks, Lee.” He threw $10 on the bar knowing most of these stiffs wouldn’t be tipping the guy.  Out of his peripheral vision, Dean saw Sam take his and slam it back in mostly one pull.  “Woah! Easy there, tiger!” 

Sam slammed the glass back down on the bar, “Refill, please.” Dean shot him a skeptical look, “Actually make that two.” He turned to Dean, “Bobby needs one.” 

Dean threw another $10 on the bar as the drinks were being poured. “Thanks again, buddy.” Sam had them in hand and was already striding back towards Bobby.  “Slow down, Sammy.  What’s got you fired up?” 

“I hate this,” He stopped and looked at Dean.  “I hate the gawking and feeling everyone watching me.  This sucks, Dean!” 

Bobby met them halfway and Sam handed the glass over.  Bobby took a swig, “A lot of commotion over where I need to be…” 

Dean interjected, “Do you need us to break it up?” 

“Nah,” Bobby took another sip, “I think we can wait it out.”

* * *

 

It was another forty-five minutes before the hall was opened for guests to be seated. They were seated with three couples, two looking retired and the others a few years older than Sam and Dean. Sam made small talk with them, careful to ask a lot more questions than answer.  It was part of the distraction thing.  Bobby had gotten up to case his potential possessed object but was currently engaged in a conversation with a woman who looked assertive, and not looking to let him leave said conversation anytime soon. 

Dean, of course, had gotten up from the table to get another drink as soon as the salad was placed in front of him.  Come to think of it, Dean had been gone a long time.  Sam scanned the room for a few frantic seconds before seeing him.  Smack in the middle of three women with one very pissed off looking man talking to Dean. He was going with the plan. Sam sincerely hoped that the pissed off man was only there to retrieve his date from the overly captivating stranger, not to pick a fight.  Sam wasn’t feeling like rolling out the barroom brawl skills in formal attire. Sam cleared his throat. “Excuse me.  I’m going to get a drink. Can I get anyone something while I’m up?” 

Evelyn, one of the retirement age women, spoke up, “No, thank you.” She smiled, “You have wonderful manners!” Then went back to the conversation. 

Sam made his way towards Dean.  He purposely acted innocent while sizing up the guy staring daggers at Dean. “Hey Dean, you need another drink?” Sam pointed to the mostly empty glass in Dean’s hand. 

“Sammy!” Dean gave an exaggerated hard slap on Sam’s shoulder.  Sam was going to punch him in the arm later for that one! “Ladies – and Bert – this is my brother Sam.” 

One of the women got grabby with him.  She ran both hands along either shoulder and down his chest, “My goodness, Sam. You certainly are tall!” 

Another woman added, “And just as good looking as your brother…” Yep, there was that predator look that Sam hates. 

Dean jumped in, “Hey! Let’s not get carried away.  Sure, Sam’s not bad looking… but we all know who the good looking brother is.” He shot a cocky eyebrow up, challenging Sam. 

Bert huffed and grabbed the woman that was still practically fondling Sam, “Let’s go, Charlene! You’re always like this when you drink.” 

Dean puffed up, “Hey man! No need to be rough with her!” 

“You want to start something!” A hard shove to Dean’s shoulder accompanied the challenge. 

Dean didn’t hesitate; he shoved the guy flat on his ass.  Sam was quick to react, grabbing Dean under the arms and hustling him out into the hallway.  “Not worth it, Dean!” 

“Son of a bitch! Let me go, Sam!” Most of the room had looked to see the commotion. Mission accomplished for Bobby’s distraction, even if it wasn’t planned. 

Dean was even more fired up once they were in the hallway in relative privacy. “What the fuck!” 

“Calm. Down.” Sam didn’t raise his voice; he didn’t need to be substituted in for that brawl Dean was itching for. 

“No! You saw that asshole grabbing her like that,” Dean punched the wall. Thankfully not hard enough to hurt himself or bust the wall.  He always had a problem with men treating women like that. It was something John Winchester drilled into their brains. “I’m going to get another fucking drink.” Killing anger with booze? That was a learned behavior.  He stormed off. 

Sam didn’t want to lose track of him.  “Dean! Wait up!” 

Dean was already to the bar while Sam was about halfway there.  Dean slammed another double as a woman in her late forties intercepted Sam, “Well you are certainly a hero.” She pushed her hands on Sam’s pecks through his shirt and felt him up.  Dean caught it and realized immediately that he had to help Sam out.  She tried to pull him towards her, “Why don’t you let me show you my appreciation for not letting tempers flare in there?” 

Dean loudly cleared his throat, “Look lady, you’re making him really uncomfortable.” 

She scoffed, “I think he can speak for himself.” And continued her attempts. 

“Aunt Sheila!” Oh thank God, there was a person who could wrangle the woman. A skinny brunette pulled the woman away from Sam.  She spoke, mortified, “I am so so so sorry about her.” She pulled Sheila with her back into the dining hall. 

Dean noticed that the woman had gotten Sam’s tie and collar crooked. Sam looked disheveled now. Dean took it upon himself to adjust it for Sam, “Jeez, get it together, Sam.” Dean pulled at his shirt collar and straightened it before adjusting the bowtie for him.  When he was done he ran his hands over the shirt collar to smooth it down, then repeated the motion over the tuxedo jacket. “I wouldn’t even feel up a girl like that when we were alone together. I don’t know what is wrong with these people…” 

Sam smiled and gave a small, “Thanks.” 

That’s when Dean noticed a gorgeous woman over Sam’s shoulder.  The woman had been watching their fairly innocent, brotherly moment with less than good intentions.  He got a good enough look at her to bring it to Sam’s attention. He leaned close to Sam’s ear, pressing chest to chest as he cast a purposeful glance over at her, “Don’t look now, but we just got someone’s attention.  Young, hot, brunette, up-do, small tits but looks like she’ll make up for it based on how she’s undressing both of us with her eyes right now… My ten o’clock, black dress.”

Sam rolled his eyes, “They’re _all_ wearing black dresses, Dean.  And how young?” 

Dean huffed, “Not barely legal or anything… looks like she should be in college though. Definitely younger than you tend to go for.” 

“So why bring it to my attention?” 

“Because as far as I know it’s been a while since you got the lead out and I’m worried your balls are gonna back up into your brain if you don’t get some action soon.” 

“Now! You want to pick this fight now? In public?” Sam pushed him away and crossed his arms. 

“Just saying…” Dean went out of his way to make eye contact with her and wink. “I mean, unless you wanted to try that thing we talked about.” 

Sam raised an eyebrow, “Good boy, bad boy? Yeah right! No one here would go for that shit, Dean!” 

“Are you kidding me? I’m pretty sure they’ve all got skeletons in their closets that would make ours blush… rich people, man.” 

The woman sauntered up interrupting their exchange. “I couldn’t help but notice you from over there.” She extended a hand, “I’m Patricia.” 

Dean pulled her hand to his mouth and kissed it, even if the hand was meant to be a shake. Sam spoke first, “I’m Sam and this is my brother, Dean.” 

Bedroom eyes didn’t even begin to describe the look she gave Sam.  “Nice to meet you, Sam and Dean.  To be perfectly honest, I was coming over here to hit on you, Dean.  Now that I’ve seen both of you I’m having a hard time deciding…” 

Sam knew exactly how he wanted to play this, “Well who says you have to?” 

She didn’t immediately throw a drink in his face.  She actually raised a damn eyebrow! Jackpot! Dean jumped in, “I mean, variety is the spice of life.  Right?” 

Sam casually slung an arm around Dean.  Now she just looked like a predator as she weighed her options, “What did you have in mind?” 

Dean played coy, “I don’t know if she’s into this, Sammy.” 

Sam stared her down, “She might be.  Depends on how adventurous she is…” 

She wasn’t having any doubts about her, “I’m not hearing any explanations, boys.” 

Sam and Dean exchanged a look, a quick silent conversation where they agreed to bite the bullet and move forward with this.  Sam started, “You see, there’s this thing we have been wanting to do.” 

Dean cocked an eyebrow, “A very sexy thing…” 

“Obviously,” Sam continued, “It’s just that we haven’t found anyone who is bold enough to try it.  You seem like you at least want to hear us out.” 

She nodded, still giving him a challenging look.  Sam moved over to her, draped an arm around her, and leaned close to whisper hot against her ear.  “We love to watch each other fuck women.  It is hotter than any porno could ever hope to be. A while back, he watched me get worked over by a dominatrix.” She shuddered with anticipation at the idea. “He says he did it for me but we learned something about Dean over there.” 

“What’s that?” Patricia was almost breathless. 

“He loves being told what to do and what a good boy he is,” Sam purred. “So we came up with the idea… just never had an opportunity to try it out.  The next time he is with a girl while I watch, I’m in control.  He only does what I say.” 

Patricia moaned, “Holy shit that’s hot.” She could feel herself getting soaking wet from the picture Sam was painting. 

Sam chuckled, “Does that mean you’re interested? You want me to bark orders while you tell him how good he’s fucking you?” 

She didn’t answer.  Instead she pulled Sam into a filthy, open-mouth kiss.  Dean was captivated by the turn of events.  She looked at Dean when they broke apart, “Why don’t you follow me, good boy?” 

She walked past Dean towards the staircase.  She must have known the layout.  Either way both were more than happy to follow her.  

She led them to a room halfway down the hallway of the second floor.  It wasn’t a huge room but it had two high back chairs, large windows with a balcony, and a king size bed with a padded bench at the end of it.  There were plenty of options on where to watch from.  Sam was the last one in and closed the door behind them.  She stopped short of the bed and turned to Sam, “So how do you want to do this?” 

Sam had to be sure. “Hold up.  Are you sure you want to do this? If you’re not on board with this I’ll leave and there will be no hard feelings.” 

She smiled, “Not everyday that a guy asks for permission.  Yes, I am completely on board with this.  The only hard feelings I’m interested in,” she cupped Dean’s crotch through his pants, “are Dean’s hard feelings.” 

Dean piped up just to reassure Sam, “You know I’m on board with it!” 

“Good,” Sam looked at her sternly, “Get your grubby paws off him until you have permission.” He pulled his jacket off and loosened his bowtie, “Sit on the bed.  Dean, I want you to strip down to your underwear.  Put on a show for her.” 

Patricia placed her small bag on the table next to the bed then got on the bed with her legs dangling off, slightly spread.  Dean was quick to toe off his shoes before she got situated. He slid one arm out of the jacket before pushing it off the other arm and fall to the floor. He let the backs of his fingernails drag teasingly over her black stockings on her thighs before moving to slowly unbutton his vest.  When he got that off he moves to the stupid cummerbund, whipping it off as quickly as possible, swinging it over his head as she giggled.  She put a hand to his chest and dragged it to his shirt cuff, “May I?” 

Dean held his wrist out as she expertly undid the cufflinks on his left side then offered his right.  She placed them on the bedside table, flicking her gaze over to Sam.  He hadn’t undressed more than he had before. He was sitting with his legs spread and elbows on his knees, studying the scene in front of him. Dean untied the bowtie and slowly pulled it from the collar.  Sam spoke, “Keep that close by.  I might want to use it later.” Dean didn’t even try to cover his shiver. She reached for Dean’s belt and Sam spoke up again, “What’d I say about being grabby!” She quickly threw her hands up acting innocent.  

Dean went agonizingly slow as he unbuttoned his shirt.  He let it slide off his body in a puddle with the rest of his clothes.  He went for his belt when Sam spoke up again, “Face me when you take those pants off. Let her appreciate that ass of yours.” Dean turned. “Good boy, Dean.” Dean blushed.  He was actually getting off on this pretty quickly. It was almost a joke when he and Sam had discussed this idea – he never thought they’d actually find someone to go through with this.  Now that it was happening it was the perfect combination of dirty, sexy, and wrong. 

Dean unzipped the fly of his pants then dragged them down slowly, bending enough to really show off his ass.  She moaned in appreciation.  Sam had a change of planned, “Lose the socks and lay on the bed.  You,” he looked at Patricia, “ditch the dress but leave everything on.” 

She couldn’t help herself she walked over to Sam, her heels clicking the floor as she sauntered over.  She turned her back to him and cooed, “A little help please, sir.” 

Sam gave her a firm open-palmed slap on the ass and she yelped.  He gave her a steely look. “Don’t play cute with me. You won’t like the outcome.” He stood and gripped the zipper on the back of her dress and slid it down. She took a few steps back and steadily slid it off her body while facing Sam.  He took a minute to take her in: neat hair still up on her head, small necklace around her neck, black strapless lace bra, with matching black lace thong, garters, thigh high stockings with black lace trim, and black pumps.  He ran a hand down her arm, “Lose the shoes.” She complied, dropping them by her dress. Sam turned her towards the bed and looked at Dean, “All of this,” he gestured up and down her body, “Stays on until I say otherwise.  Got it?” 

“Got it,” Dean replied.  God, he sounded wrecked already. 

Sam leaned down to whisper against her ear again, “Go over there and straddle him. Make sure you rub these pretty panties against him as much as you can.” 

She didn’t need to be told twice.  She went over, climbed onto the bed then crawled over to Dean’s body. She straddled him and rubbed her crotch over his stomach, he groaned loudly in response.  Dean never told Sam about his panty kink, but the fucker figured it out all on his own! “Can I please kiss her, Sammy?” 

“Go for it.” 

Dean pulled her down and absolutely plundered her mouth.  He knew Sam would just demand that he be rougher if he didn’t start that way.  He had a hand that kept getting stuck in the pins of her hair; eventually she huffed and pulled back.  She made quick work of yanking ten pins out of her hair before tussling it with her fingers, making it wavy and messy.  Dean couldn’t wait; he weaved both hands into it and pulled her in for another sloppy kiss as she ground small circles against his erection.  He could feel her soaking through his own boxers and that was almost his undoing.  

As if Sam could read his mind, “I want you to switch it up.  Dean, lose the boxers. Trish, I want you to lay down now.” 

She rolled off him and Dean yanked his boxer briefs down.  His aching hard on smacked against his stomach as he dragged them the rest of the way down.  Sam got closer to the bed, Dean noticed that he had taken most of his clothes off; he was down to socks and pants with no belt.  Sam leaned against the bedside table. “Now, you’re going to keep making out with her, but feel free to rub all over those wet panties with your dick.” He punctuated with a smug grin.  

Dean was conflicted with feelings: turned on, embarrassed, nervous… it all sent a thrill down his spine.  Dean scooted between her legs on his knees before draping himself over her. He placed a small kiss between her breasts before licking along the edge of her bra and moving to her shoulder.  He kissed his way from her shoulder to just below her ear and gave the first tentative roll of his hips against her.  She let out a loud moan and her fingers dug into Dean’s arms.  Sam was still leaning against the table, stroking himself through his pants, “Tell him if he’s being good.” 

She arched up into Dean, “So good!” Dean thrust against her this time and she moaned again, “You’re such a good boy, Dean!” 

Dean moaned low in his throat and took her lips in his again.  He sped up his thrusts as he felt her continue to grow wetter.  Her inner thighs were slick, and it was driving Dean crazy.  Sam spoke up, “Good boys hump a little harder than that.” Dean thrust harder and broke away from Patricia’s lips with a long, loud groan. “So good for me, Dean.” 

Dean couldn’t even be mad at how smug Sam sounded.  He was going to end up blowing a load at this rate. Judging from the way this woman was panting underneath him, he was pretty close to getting her off too. “So good – oh my God – Dean!” She was grabbing at anything just to ground herself. 

Dean pulled back and looked her in the eye. “You close?” She nodded enthusiastically. “Good.” He turned to Sam, “Please, can she come?” 

Sam leaned closer, “Only if you keep it up like this.” 

Dean redoubled his efforts.  He thrust against her just like he would if he was inside her.  Ruined panties dragged against him with every stroke. He was huffing hot breaths against her neck as one hand stayed in her hair and the other went to rolling her nipple through the material of her bra.  One hard thrust and a pinch to her nipple simultaneously is all it took to send her over the edge.  He felt the gush of warmth over himself.  Sam spoke, “Fuck her through it.” Dean kept rutting against her. “Good boy.” 

She was writhing under him, “So good, holy shit.  So fucking good.” 

Dean could feel the tension in his entire body; he was hanging on by a thread. It’s completely possible that he’d die from this, at least in Dean’s opinion.  He kept his motions up, rubbing his aching, hard dick against her in a teasing promise of what was to coming but it was overwhelming him. Feeling the smooth, textured drag of her thong against him was too much.  He didn’t even feel embarrassed as he started whimpering instead of grunting as he sucked hickies against her neck rutting hard enough to chafe at this point.  That’s when Sam decided to push the issue, figuratively and physically, by crouching behind Dean and leaning over him, bare chest to back, to lean in over Dean’s ear, “What’s wrong, Dean? Too much for you?” 

It didn’t matter to Dean at the time if it was his brother or not, he pressed back hard into Sam’s body and let loose a needy, embarrassing noise.  The woman below him spoke up before Dean had the chance, “Come on! Let him fuck me!” 

Sam chuckled darkly, the rumblings of it tickling on Dean’s back, “Don’t you mean, ‘Let him fuck me, please?’ The last time I checked you signed on for me to be in charge too.” 

She arched her back and ran a hand from Sam’s shoulder to the top of his hand, “ _Please_ let him fuck me.” She put an exaggerated moan on the end for emphasis.  She was a terrible actress, but Sam was tired of playing this part of the game. 

Sam slid off the bed and grabbed Dean’s pants.  He rummaged in the pockets and pulled out his wallet, producing a condom from it.  He handed it to Dean, who took that as instruction to roll it on.  Sam dropped his pants and climbed on the bed lying about a foot from Patricia. “Here’s how this is gonna go: Dean is going to fuck you, but only by moving those wrecked panties to the side.” 

Dean moaned, “Please Sam, I can’t –” 

“You can and you will! You’re gonna feel them against you the entire time!” He started stroking himself through his boxers, “And I’m just going to lay here and jerk off…” He turned to the woman, “If that’s okay with you.” 

“God yes!” She dragged Sam into a sloppy kiss.  He didn’t stop her. 

Dean gently pushed her thighs further apart and hooked his fingers into the soaking lacy just above her clit.  He yanked them aside and indulged himself in one long, smooth lick from her hole to her clit while Sam was distracted.  She moaned and deepened her kiss with Sam.  Dean wrapped one of her legs around his lower back and gripped the base of his cock as he slowly pushed into her.  She broke the kiss with a groan, “Holy shit – you’re huge!” 

Dean stopped immediately, “Do you need me to stop?” 

“No! I just need you to speed it up.” 

Sam had a devilish grin, “Yeah? You want him to punch that gigantic dick of his into you and make room for himself?” She moaned.  Dean didn’t move yet. “He’s gonna need an answer sweetheart. He is a complete gentleman. Good boys don’t wreck girl without permission.” 

“Shit, yes! Please! Fuck me open like a good boy!” 

Dean shot his eyes over to Sam, he was completely unsure with how Sam wanted this to play out.  Maybe Sam wanted her to beg more.  Sam got a dark look on his face and jerked her chin down to look at where Dean had just the tip of his cock inside her.  “Look at that.  Do you have any last words for your pussy as you know it? Because you’re never gonna be the same once he splits you open and rips an orgasm out of you.” 

Dean could feel her gush more slick onto him as she tightened.  She panted, “Please. I want that! Want him – please sir, let him fuck me! Please!” 

There it was.  “Fuck her good and hard, Dean.  Fuck her like I would. Make sure her body never fucking forgets you!” 

Dean steeled himself.  He really wasn’t a fan of being rough, especially on initial penetration.  He liked to finger a girl then slowly go in but he knew that wasn’t Sam’s style.  He snapped his hips forward but not all the way to the base, not yet. All the air in her lungs punched out and she gripped one of Dean’s arms and one of Sam’s.  “You good?” Dean was tentative. 

“Fuck yes! So good…” Her grip on his arm tightened as he pulled back a little and shoved the rest of the way in.  Her eyes rolled back as she felt herself get filled.  Sam slid back to shove his boxers to the middle of his thighs.  

“Sammy can I change this position a little? For her?” 

“Sure thing.” Sam turned to Patricia, “See he’s thinking about how to make it good for you.” 

Without hesitation she looked Dean in the eye, “Good boy.” 

This time Dean blushed as he picked her hips up.  He wrapped both legs tightly to his waist and kept her butt and hips off the bed.  Dean was on his knees, giving him more leverage.  He kept a strong grip on her hips as he snapped forward again. This time she was seeing starts. Dean didn’t let up this time. He hammered his hips in quick, hard thrusts.  She was moaning loudly and grabbing at everything.  Sam even let a stray moan out as he watched Dean.  Dean kept his pace but looked at Sam, “A little help?” 

Sam gave him a look, not sure where he was going with that.  “With?” 

“Rub her clit? Do it hard and fast? I can’t do it from this position without dropping her… please.” 

That fucking fucker’s request almost had Sam blowing his load.  He gripped the base of his cock hard to stop that from happening.  “Holy shit, Dean.” He brought two fingers to his mouth and licked across them. He got on his knees next to her hip and brought them down to her clit, rubbing back and forth quickly. She arched even more as they worked together.  She grabbed Sam’s thigh, nails digging into the skin.  The two working in tandem didn’t take long.  She came with a strangled cry.  Dean pulled out so she could gush on him and immediately went back to fucking into her when it stopped.  Sam kept up his motions, occasionally stopping in favor of fast, firm slaps directly against her clit.  He had his other hand furiously pumping his own dick. She was thrashing underneath them. Her inevitable third orgasm ripped out of her comically fast.  

Dean changed position again.  He grabbed her legs and put them over his own shoulders and bent over her. She was practically doubled onto herself as Dean fucked down into her.  

Sam went back to lying down and panted, “Make her come one more time, good boy. Then you can come whenever you want.” 

Dean reached a hand down to rub circles over her clit as he continued going to town on her.  She was thoroughly debauched.  Dean saw that look on her face; he’d seen it plenty of times.  The moment that it dawned on her that he’s giving her the best sex of her life.  Dean huffed out, “You’re welcome.” 

Her entire body went slack before clenching around him one more time.  She didn’t make a sound as her eyes rolled back and she went slack again.  That was it, her brain checked out for the moment.  Dean thrust a few more times before slamming home, balls deep, and coming. Sam finished right behind him coming over his own hand and stomach. 

Dean lowered her legs and gingerly pulled out before taking the condom off and tying it up. He flopped back on the bed with his head resting against Sam’s legs.  All three continued panting for a few minutes.  Sam was the first one to get up, taking his boxers off and using them to clean himself up.  He was walking over to retrieve his pants when the door to the room flew open. 

“Sam? Dean? Are you – WHAT THE?!” 

Shit. Bobby. 

Sam froze like a deer in the headlights, stark naked except for his socks, crouching to get his pants from the floor.  Dean flew up to a seated position on the bed as Patricia scrambled to cover herself. Dean had better reaction timing, “Shit! Bobby we can explain!” 

Bobby slammed the door, “I don’t wanna fucking know!” 

Dean flew off the bed and yanked his pants on.  He caught up to Bobby just before the stairs, “Bobby! WAIT!” 

Bobby turned, clearly angrier with them than Dean has ever seen.  “We are gonna talk about this.  Just not here.  Not now.  I’ll get a cab back to the motel.  Don’t rush on my account.” 

“So you got the thing?” 

Bobby stormed down the stairs without answering. 

When Dean got back to the room Sam was zipping up Patricia’s dress.  Awkwardness was a heavy curtain over the room. One look at her would tell you what she was up to that night with the disheveled hair and messy makeup. “I’m really sorry about that.” 

She walked over to the table and got her purse then stormed out of the room past Dean without another word.  Who could blame her? 

Sam sat down in a chair and buried his head in his hands, “Shit.” Dean rubbed his shoulder but said nothing.  “What are we gonna do, Dean?” 

Dean squeezed Sam’s shoulder.  “We’re going to get dressed.  We’re going to get the car.  And when we get back to the motel we’re going to get the reaming of a lifetime from Bobby Singer.” 

Sam groaned and buried his face further. “We fucked up.” 

Dean sighed, “Yeah.  We did.”

* * *

 

When they got back to the motel they changed clothes and went immediately to Bobby’s room. Bobby had made a significant dent in his whiskey bottle since getting back to the room.  Some things just can’t be unseen.  Of course the boys would be doing something freaky with each other, they were always unnaturally close growing up practically homeless. Hell, that’s why Bobby would regularly give John shit for not settling down in a regular home. 

The tentative knock at the door pulled Bobby from his thoughts.  He took a deep breath and opened it, knowing it was Sam and Dean.  Both boys had their heads down and were braced for an explosion.  They had both changed into jeans and button-down shirts with dark shirts underneath, ‘Christ they even dress alike,’ was all Bobby could think. He gestured for them to come into the room. 

Neither boy looked at him as he walked in front of them, examining them. “Either of you mind telling me what the hell I walked in on?” 

“Look, we’re sorry we fucked up and weren’t there to back you up –” Dean started. 

“Fuck the hunt! Your tussle during the salad portion gave me the distraction I needed to get it done.” Dean let out the breath he didn’t realize he was holding. “I’m talking about what I walked in on upstairs – and don’t think about lying to me because I think we’re all old enough to know the god damn _smell_ of the room was enough to give you away!” 

Sam cleared his throat, “This woman came onto us – both of us – after Dean had that dust up.  She was completely consenting, just really pissed and embarrassed afterward after you… you know.” 

Bobby eyed him suspiciously, “So you both had sex with her?” 

Dean interjected, “No.  I had sex with her and he watched… well for the most part.” 

Bobby was getting agitated, “For the most part?” 

Dean shifted back and forth, “Well I did most of it, but asked him to help with… Jeez! Are you gonna make me give you a whole play-by-play?” 

Sam stepped in, “No one’s getting hurt and it’s just a thing we do…” 

Bobby was confused now, “A _thing_ you do?” 

Sam was fidgeting now too, “Well not like often or anything.  Just once in a while one of us will pick up a girl and…” 

Dean bit the bullet, “Sometimes we get our rocks off watching each other fuck girls. Like porn but live action.” 

Bobby’s jaw dropped.  He needed a minute. No, he needed another drink. After a long pull directly from the bottle he spoke, “So one of you idjits picks up some woman and the other just… what? Sits there and masturbates?” Both brothers nodded. “That is not a thing! That is not a thing that people do!” 

“It’s a thing, just… taboo,” Sam rationalized. 

“Shut up!” Bobby took another drink, “It’s ‘taboo’ because you are related. Flesh and blood.” 

“The women are always into it,” Dean offered. 

“Of course they’re into it! You’re both good looking and they’re never seeing you again after the deed is done,” Bobby looked at Dean seriously, “Did you Dad know this stuff was going on?” 

“No! God, no,” Dean’s heart was pounding in his chest, “Dad knew as little as humanly possible about my sex life.” 

Bobby stared at them for a long time, analyzing and trying to figure out what to say next, “This is not okay.  This thing you’re doing.  I get that you don’t think it’s wrong but it certainly ain’t healthy for either of you.” 

“Understood,” Sam responded. 

“Got it, sir,” Dean was still fidgeting and looking at the ground.  

“Now, one of you idjits go get me another bottle of this,” Bobby held the whiskey up, “I’m gonna drink until I hopefully forget what I saw today.  You two are welcome to join me as long as you keep your hands off each other.” 

“I got it!” Sam couldn’t have grabbed the keys out of Dean’s hands fast enough. 

This was awkward.  Someone was bound to call them out eventually.

**Author's Note:**

> First: never never NEVER use condoms that were stored in a wallet. For whatever reason a lot of people are unaware that the body heat from being in a wallet makes them less effective and therefore less safe. 
> 
> A comment on a previous installment gave me the idea for this but I used gif inspiration for the actual text. In this case, I had three in mind but I only ended up using one in the text. Meander over to Tumblr and give a heart. I don't own anything I'm just a curator of porn gifs (apparently).  
> http://sexience.tumblr.com/post/127494768624/best-porn-blog-ever  
>   
> http://sexience.tumblr.com/post/127348552087/best-porn-blog-ever  
>   
> http://sweet-loving-sex.tumblr.com/post/125808856625/sweet-loving-sex  
> 
> 
>  
> 
> I waffled on whether they would be caught by Bobby or John but felt Bobby was more impact. Thoughts?
> 
> Any prompts/suggestions for the boys continued sexcapades is welcome!
> 
> As always kudos, comments, and constructive feedback are always welcome and encouraged!


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